Benzoyl chloride → HCID 118353918, compound

Participants

Reaction Steps

A solution of {(S)-1-[(S)-1-((S)-2-aminomethyl-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carbonyl)-2-methyl-propylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (intermediate 3) (100 mg 0.23 mmol) in DCM (4 mL) was cooled to 0-5° C. and triethylamine (0.08 mL 0.57 mmol) followed by benzoyl chloride (0.027 mL, 0.23 mmol) were added. The reaction was stirred at rt for 4 h. The reaction mixture was partitioned between water and DCM and the organic layer was then washed with water (30 mL×2) and brine (30 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by preparative-HPLC (acetonitrile and NH4OAc] to give ((S)-1-{(S)-1-[(S)-2-(benzoylamino-methyl)-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carbonyl]-2-methyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester as a white solid (35 mg), m/z=538 (M+H).

Provenance & Evidence